Navigating Ambiguity: Insights from Himanshu Palsule, CEO of Cornerstone

Ambiguity can be unsettling and uncertain, but it can also be rewarding.

I remember the day I left behind my established corporate job in Bombay to move to San Francisco to join a startup. That feeling of adventure mixed with trepidation. Equal parts eager and terrified. That ambiguity, as I boarded my long flight on December 31, 1989, with $150 in travel allowance and an address in Walnut Creek, California, where my wife and I were on assignment, has played a big role in my career choices. It has also made for those great fireside immigrant stories that my children have long tired of — how we made it to the US with two bags and a couple hundred bucks driven by an unseen force of ambition and adventure.

To me, ambiguity is that feeling you get when you aren’t sure where the path ahead of you leads, but you still feel a strong tug. It’s an uncertain step into the dark and a force that draws you to keep seeking. You’re never 100% sure what will happen, and you go forward anyway because you know that confronting ambiguity is the best way to grow.

Throughout my career as a leader, I’ve found that you can’t force someone to take that step into the dark. Instead, you have to create a safe, supportive environment that fosters confidence so your people feel empowered to take those steps on their own into the unknown. It’s my job to lead through ambiguity and mitigate the fear it can cause my people. As the CEO of Cornerstone, I work to shift how people feel about the ambiguity of the future from scary to exciting by building paths forward every day. And I wanted to share with you some personal journeys that will hopefully motivate you to support your people when they face ambiguous situations.

Leading through ambiguity, for me, is about navigating uncharted territories with a blend of available data-driven analysis and instinctual decision-making.

When I left behind the familiarity of my job in India and ventured into the dynamic world of the ’90s San Francisco startup scene, the transition was not without its challenges. It was a different world back then, where the forces of globalization flattening the world and making it more homogenous were in their nascency. My wife and I were assigned projects in big towns and small towns in America, which in itself created a sense of ambiguity to my own identity. I remember the day during the Iraq war in a small town in Colorado when our project manager walked up to us and hoped our families were safe in India since — to her — it was part of Iraq. We learned the joys of happy hours, took to the other football right away (I’m still a diehard 49er fan), and appreciated the grit and determination of the American people and their outlook on life. And to my wife and I, it soon started to feel right. We started realizing that this could be our forever home, which was a huge step given the comforts of a more predictable life we had left behind.

To be a leader when you aren’t sure what the future looks like requires continuous and collective adaptation and learning. Look at what happened in March 2020, when entire workforces had to leave their offices to work remotely for what we thought would be a couple of weeks to slow the curve of the pandemic. Many of them, even today, have not returned. Being a leader, you have to draw upon your history and the diverse perspectives and experiences of the people around you to inform your decisions. But still, as a leader, it’s always on you to make the choices. It gets lonely quickly making decisions during ambiguous times.

My time in San Francisco was at the peak of the early ’90s tech boom, and I was eager to join the digital gold rush during immense growth and discovery. But it wasn’t easy because thriving amidst uncertainty takes work. I learned that outstanding leadership balances available information and gut instincts while remaining acutely aware of the situational context. And it helped shape how I lead through ambiguity today and how I want my leadership team to lead, too.

That was just the first of my many moves throughout the US. Each new environment brought its own challenges, from the dynamism of Silicon Valley to the chill of Minnesota winters balanced by the warmth of the Midwest culture, and the “federal world” of Washington DC to navigating LA traffic (I’m still not sure which one is easier to handle). Along the way, I navigated personal milestones, like starting a family while completing a Master's degree, and learned that adaptation isn’t just about you, but it affects the people you care about, too. And, through it all, I embraced ambiguity as a catalyst for growth, trusting my instincts and learning from every experience and everyone around me.

The ability to lead through ambiguity is more critical than ever. We live in an even more uncertain world today than I have ever experienced, and the pace of change is more rapid than anything I’ve seen before in my career. All the while, the world of work keeps getting flatter as organizations get more diverse and global, and teams are divided across time zones, countries, and continents.

Leaders today have to think globally and socially because both are now congruent with successful leadership. Embracing uncertainty as an opportunity isn’t just nice to have; it’s absolutely essential for growth, transformation, and success. We are in a world where social platforms have the ability to instantly judge your decisions, where information flows freely, and where your personal choices are always public. Now, you are being watched and followed during ambiguous times.

Reflecting on my journey, I believe three critical leadership skills are essential for leading through ambiguity. Cultivating curiosity, increasing situational awareness, and embracing courageous leadership are the key pillars of my approach.

Remaining curious and open-minded is essential. Don’t get comfortable with your default. Uncertain circumstances call for unorthodox thinking. Don’t be afraid to challenge assumptions and explore unconventional solutions. Always look for a better way to solve a problem.

The more you can take in about a problem, the better your chance of finding what you need to solve it. Understanding the broader context is vital because the situation is often more important than the solution. For example, during the many acquisitions I’ve been a part of, when acquiring a company, what you get in totality is often different than what you expected. Success requires situational awareness to stay agile in your decision-making as you adjust to cultures, expectations, and all the other aspects you can’t cover on a PowerPoint slide.

Leading through ambiguity is not a popularity contest. Having the grit and conviction to stand alone and advocate for what is right, even in the face of opposition, is essential to all forms of leadership. The ability to say no is more impactful than the urge to agree. Sometimes, the choices you make for your customers may not immediately be intuitive, but they are the right ones. Like when Apple saw Blackberry at the height of its popularity and decided their phone would remove the physical keyboard. And sometimes, you might not make the right choice, but you know that not making a decision during a time of change can be more harmful than making the wrong one.

With curiosity, situational awareness, and courage — I’ve discovered that you can make it so “positive change is the only constant.” It’s not always easy, but it is always possible.

At Cornerstone, we’ve taken proactive steps to address ambiguity in the workplace. Prioritizing open communication, embracing diversity, supporting flexible work, and accommodating the evolving needs of our people have been crucial. We’ve fostered a culture of resilience and adaptability by listening to our employees, leveraging technology, and staying true to our organizational values.

As for myself, I rely on personal practices to maintain focus and clarity. Aligning decisions with core values and moral principles guides my approach to navigating ambiguity. Deep breathing techniques help me stay grounded and centered while seeking out relevant expertise and drawing on my past experiences has also provided valuable insights. They also help me filter out the loud, obvious signals to focus on the weak signals that oftentimes make for successful decisions. Weak signals are the less obvious tells of what will make someone or something a success.

The ability to spot and act on these weak signals often makes the difference. While CEOs were making decisions on getting people back to work post-pandemic and there was plenty of data on “Zoom fatigue” and the benefits of getting back to the office, I acted on weak signals to allow for fully flexible, remote work and still do. These weak signals were things like traffic issues in places where we have offices like Mumbai and LA, making for impossible daily commutes, or geopolitical challenges facing our Poland and Israel workforces. Reading our internal Slack channels on how employees were managing remote work, it just felt right to me.

In the ever-changing landscape of modern business, ambiguity is not a barrier but a catalyst for growth and innovation. Cultivating curiosity, increasing situational awareness, and embracing courageous leadership are key to guiding your teams through change and uncertainty. As leaders, we are responsible for building an environment where our people have the confidence to listen to their weak signals and make their own choices, empowering our teams to navigate ambiguity with support and resilience.

Throughout my career, ambiguity has been a constant, showing me the transformative power of embracing uncertainty and leading with courage and conviction. So, let’s embrace ambiguity as an opportunity to chart new paths, inspire our teams, and drive meaningful, positive change.